Windward Cay Holidays

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    Save up to NZ$2,400 when you book a flight and hotel together*

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Our guide on where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods for the activities you enjoy most. Learn more about Windward Cay
The entrance to the Hollywood Studios area with a large sign and distinctive architecture.

Bay Lake

4 out of top 10 points of interest in this area

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

Find hotels in Bay Lake

Our pick of the best Windward Cay Hotel Deals

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
The price is NZ$438 per night from 23 Nov to 24 Nov
NZ$438
23 Nov - 24 Nov
includes taxes & fees
9.4/10 Exceptional! (4,613 reviews)
"Una propiedad excepcional"

Reviewed on 14 Nov 2026

Hyatt Regency Orlando International Airport
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is NZ$226 per night from 15 Dec to 16 Dec
NZ$226
15 Dec - 16 Dec
includes taxes & fees
9.2/10 Wonderful! (7,328 reviews)
"Solid clean functional Unit great for Disney access without the Disney prices."

Reviewed on 14 Nov 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
The price is NZ$195 per night from 15 Dec to 16 Dec
NZ$195
15 Dec - 16 Dec
includes taxes & fees
Marriott's Grande Vista
See all 55,672 properties in Windward Cay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Windward Cay holiday package cost?
Tailor make your Windward Cay holiday package from just . Pick from any combination of flights, hotels and rental cars to pull together the trip of your dreams. Don't forget to add on a few experiences or activities!
How do I get a cheap travel package to Windward Cay?
Bundle your bookings with Expedia to save big on your next getaway. With more than 550 air carriers and 1 000 000 hotels throughout the world, your Windward Cay holiday package can be tailored exactly to suit your budget. With all those extra dollars, why not add one or more interesting experiences and tours? It's an easy way to unlock even more savings. Your dream holiday in Windward Cay is much closer than you thought!
Where should I stay in Windward Cay?
A trip to Windward Cay isn't complete without stopping by Old Town, Fun Spot America and Give Kids the World Village. Spend your evenings near these popular attractions and make sightseeing a breeze.
What are the top hotels in Windward Cay?
Make a reservation at Ref 43 Family Villa With Own Pool Near Disney. It's one of the neighbourhood's most in-demand properties. Another top-rated option in Windward Cay is Lakeside Villa With Perfect Views From Your Private Pool In A Peaceful Community.
How far in advance should I book my Windward Cay holiday?
Reserving your spot early with Expedia means one less thing to worry about. Most air carriers advertise prices up to 12 months prior to departure dates. Usually, this is the cheapest time to book. If circumstances have left you booking late, great deals to Windward Cay will sometimes occur just a few weeks before departure.
What does an Expedia Windward Cay travel package include?
Much of that is up to you. You can select from a variety of Windward Cay packages, such as a rental car, flight and hotel. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your perfect Windward Cay trip looks like, get set to save!
What should I know before booking a Windward Cay travel package?
Bundling your bookings into a Windward Cay holiday package is the easiest way to organise your trip. Not only that, you'll save when you combine your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
If I'm not able to travel, can I cancel my Windward Cay holiday package?
Your situation can change unexpectedly, so yes, you can. You may be able to change or cancel your Windward Cay holiday package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make changes, but your car rental company, airline or hotel may impose a charge. Need more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Activities

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

NZ$59
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

NZ$48
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

NZ$347
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
See all activities in Orlando
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.